Diethyl Malonate → 1,3-Diethyl 2-(3-oxocyclohexyl)propanedioate

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Reaction Steps

A solution of 30 ml of 2-cyclohexen-1-one in 35 ml anhydrous ethanol is added dropwise at a temperature below -10° to a reagent prepared from 0.1 g sodium, 100 ml of absolute ethanol and 50 ml of diethyl malonate. The reaction mixture is allowed to warm slowly and is stirred at room temperature overnight. The mixture is evaporated to dryness, the residue is dissolved in ether, the ether solution is washed with brine, dried, filtered and evaporated to dryness. The residue is distilled under reduced pressure to yield diethyl 3-oxocyclohexylmalonate, b.p. 147°/0.5 mm.

Provenance & Evidence